Sissy Life: Sissy's New Tray

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Sissy gets an unfortunate tray 'upgrade'.
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It's funny what you get used to. I've been my wife's live-in sissy maid for almost 6 months now. Her lover lives with us. He shares her bed. I'm used to that. I'm used to him fucking my wife regularly and I'm used to him fucking me occasionally. I'm used to sucking him off daily; I'm used to the taste of cum. I'm used to the funny looks I get from delivery people when I answer the door in my full maid uniform. I'm used to being spanked for any mistakes I make. I'm used to the chastity device I wear 24/7. I'm used to begging to be allowed to masturbate and I'm used to being told no. I'm used to walking in heels. I'm used to being told what to wear and what to do by Mistress and Sir all day, every day. I'm used to hurrying to the sound of the bell that's rung to bring me to attention. I'm used to being a sissy and not Mark anymore. I'm *not* used to Friday nights.

On Saturdays my Mistress & Sir go out. They go to different places, but the routine is always similar. Mistress has a bath. I draw it and I wash her and dry her and dress her. Sir showers. He showers alone. Whilst he showers I iron his outfit. Usually a suit and casual shirt. I dress him upon instruction. I polish their shoes before they go and lastly, just as they are leaving, they give me list of chores for the night. This differs from my standard chores. This is an adhoc list pulled together to 'keep me out of mischief' whilst they are out. I'm in bed before they return. I'm used to that. I'm *not* used to Friday nights.

It's Friday night tonight. On Fridays Mistress and Sir stay in. They stay in, eat a takeaway, watch something on telly and drink. It's the drinking that means I can't get used to Friday nights. I never know how the evening will go. Sometimes nothing of note happens. More often, there's some sort of...incident. When you are the sissy of the house, incidents tend to be bad news. I got my tattoo after a Friday night. My tongue piercing too. And my nipple piercings! All as a result of some Friday night madness. My website went up after a particularly wild Friday night.

Right now I'm in the living room wearing my 'guest' uniform. It's a classically styled French Maids uniform, but instead of being black and white it's pink and white. I used to wear this whenever Sir stayed over. Since he moved in I only wear it when instructed. I was instructed to wear it this morning. I'm also wearing pink, 4-inch heels, white stockings and a pink garter belt. The uniform is short with a circle skirt trimmed with lots of white lace. The petticoat underneath pushes the skirt out giving it an even shorter appearance. Today the skirt is pinned up revealing my red bottom. I was spanked this afternoon for failing to swallow all of Sir's cum. It really wasn't my fault, but that didn't stop the spanking.

The uniform has large puff sleeves with large ribbon bows. The bodice laces up at both sides and across the front creating a bib effect. It's finished with more lace around the neckline and satin bows to the front, covered with a white small apron. I'm wearing a matching pink hat that says 'sissy'. The uniform is locked at the back of the collar. Sir has the key. He has the key to my chastity device too these days.

I'm wearing my usherette tray too. It's a large wooden tray like ushers had at the cinema or the theatre in the 50s. It has 'Maid to Serve' etched into one side. There is a strap that goes over my head and a buckled belt that goes round my waist. It isn't locked on me, but it might as well be. I wear it at all times. I am expected to make 'use' of it for all my chores. It's not useful, it doesn't help - at all. I can't see my feet so it makes walking more difficult and other than that it just gets in the way. Sir likes it though and what Sir likes he gets. I have to polish it every evening with a special kit that I got as a birthday 'present'. Sometimes Sir makes me polish it after I've used it to 'assist' in the bedroom too. There's really no need. It hardly gets dirty as I stand there with lube and condoms on it whilst he fucks my wife. As I say, what Sir likes Sir gets.

Right now my tray has two things on it; the bottle of wine Mistress is drinking from and a decanter that holds Sir's whiskey. I'm knelt next to the chair they are snuggled up on. My back straight, the skirt of my uniform neatly fanned out around my knees, my red bottom on show. I'm holding my pose steady. I know better than to slouch. My back and legs are aching. I've been like this for hours.

Sir runs his finger along the side of my tray.

"You like your tray don't you sissy?" I tell him I do, even though I hate it. "I'm thinking of getting you another. For special occasions. Look here."

He shows me a photo on his phone. The untrained eye likely wouldn't notice the difference, but I can see it's a different type of tray. It's smaller. It looks much less cumbersome. He asks me if I like it and I tell him I do. I'd tell him that even if I didn't! He scrolls through a few more photos. It's definitely smaller. I can see on a photo taken from over the shoulder of someone wearing it that it sits higher up. It looks like it's just big enough to hold two cups of tea. There's a buckle round the back like mine, but no strap over the head that I can see. Any time wearing that would definitely be better than wearing the one I've got on now! Or so I think. He scrolls to another photo and my heart sinks. This photo is taken from the front. It's being worn by a sissy. At first they look almost passable, but I can see the hint of a chastity device so I know they're a sissy. Like me. The tray is clearly smaller and it does sit higher, but now I see why it doesn't have a strap that goes over the head of the person wearing it. From the two corners of tray that sit away from the sissy's chest run two chains...which attach to the sissy's nipple rings. Suddenly I doubt this tray would be more comfortable than mine! I can see the sissy in the photo grimacing and they don't even have anything on their tray...

For a minute or two neither my Mistress nor her lover say anything. They just let the revelation sink in.

"Aren't you going to thank us?" my Mistress asks."We spent a long time finding that for you".

Mustering as much gratitude as I can I thank them. Being careful to balance the bottle of wine and decanter on my existing tray I move in front of the chair they are sharing, look up at them and with deep sincerity (that I don't feel) I ask if there is any way I can repay their kindness. Sir says not and that, in fact, after I've cleared the stuff in the kitchen away I can retire for the night. Apparently I have a busy day tomorrow for the fitting of my new tray. Neither of them make any effort to unlock my uniform so it seems I'll be sleeping in it tonight.

I didn't sleep much that night. I was nervous. That tray looked uncomfortable and I didn't know where the fitting was going to be held. So far I had only been exposed as a sissy to my Mistress, her lover ('Sir'), the odd taxi driver and delivery man and TJ, the tattoo and piercing guy. I wondered if this would be another trip to see TJ; not knowing was making me worry.

I was awake when my alarm went off. I got up promptly so as to avoid getting behind. Today seemed like a bad day to get into trouble. I couldn't shower with my uniform still on. So I freshened up as best I could.

In the kitchen I checked the breakfast orders. Thankfully they had kept it simple; avocado and eggs for my Mistress, blueberry pancakes for Sir. I had breakfast whipped quickly and was in good time when I knocked on their bedroom door.

"Come in". As I entered I was pleased to see just my Mistress in bed. The shower was running so that's where Sir was.

"Breakfast is served Mistress" and I curtseyed. "Would you like coffee up here?". I had the coffee pot and two cups on my tray. Mistress said she and Sir would come down. I curtseyed (quite a task balancing things on my tray!) my understanding and went back downstairs.

I poured two coffees out and stood to attention by the breakfast bar, back straight, chin up waiting to serve them both. Mistress was down first. I carefully curtseyed again and she took her coffee off my tray and sat down. I presented her breakfast and she set about eating. When Sir appeared he seemed eager to increase my nervousness about the day ahead. He took his coffee, had a sip and placed it back on my tray. It was going to one of those mornings where I acted as a glorified coaster for him. Checking he was okay without his coffee for a moment I fetched his breakfast.

As he took his breakfast from my tray (but leaving his coffee) Sir said, "have you seen your outfit for your fitting?"

I said I hadn't and he just smirked. I was getting panicky. The rest of breakfast passed largely uneventfully. Once they had both finished (Sir taking an extraordinary amount of time to drink his coffee I thought), I loaded the dishwasher. I figured it wouldn't be long before my Mistress showed me the outfit I was now dreading. Almost on cue Mistress popped her head back in the kitchen said when I was finished I should meet her in the Master Bedroom. That too used to be my bedroom.

"Kneel down". I kneel so Mistress can unlock my uniform. I've been instructed to shower and then put on the outfit in the suit carrier on the door. I don't know what's inside the carrier yet. I shower quickly and having dried myself off unzip the suit carrier. Inside appears to be a standard French Maid uniform. It's not my usual one - the sleeves are different - but it's essentially the same. I'm relieved. I start to dress. I always dress in the same order. Sir has specific views on not only what a sissy should wear, but also how a sissy should dress. It's always; stockings, garter, heels, bra, uniform then uniform accessories (apron, hat etc.).

I pop the black stockings on first, then the white garter carefully attaching them so there are no runs and the seams at the back are straight. Then the black 4 inch heels. The bra is next; it's a peephole bra which is unusual but not unheard of. As usual there are no pants to hide my chastity device. I hope the uniform isn't too short. I take the uniform out of the carrier and give it the once over. It looks fine. I step into it and lace it together at the front. I adjust it so it sits smooth and then I realised the trick of it. To compliment the peephole bra are small two holes around nipple height of the uniform. It didn't take a genius to realise my nipple rings were expected to be pulled through. I gently pull them through.

I head downstairs not knowing what's happening next. I hope I won't be leaving the house like this.

"Sissy! Come and meet Anthony, he'll be fitting your special tray today". Anthony is tall and lean. He's handsome and I feel very foolish being introduced like this. I know what's expected of me though and by way of an introduction I grasp the corners of the skirt of my uniform and bow into a deep curtsey.

"Where would you like him?" Mistress asks Anthony and Anthony says over by the window where the light is best would be good. First Anthony inspects my nipple rings. Satisfied that they suitable he opens a brown package. The tray inside is oak in colour. Anthony pulls it out and fastens it around my front with the buckled belt. As in the photos it sits higher than my current tray. He checks with my Mistress that she's happy with how it sits. The belt seems to be holding the weight of the tray easily. Anthony takes out two chains. First he attaches them to the corners of the tray that are away from me. Then one by one he attaches them to my nipple rings. Again he checks that my Mistress is happy with how it looks. She says she is, but wants a demonstration.

"Serve us coffee sissy." and with that I'm dismissed to the kitchen.

As the coffee brews I try to adjust to my new tray. It does feel more comfortable, but I'm worried how it'll feel when it has things on it. I place two empty cups on it as a trial and immediately the tray pushes down, the chains pulling taut on my nipples. It's all I can do not to yelp out loud. God knows how I'll cope with the cups filled. I take the cups off, pour the coffee in and gently place them back the tray. The pain through my nipples is excruciating! I have no choice but to manage. I grit my teeth and walk - and softly as I can - back into the living room.

"Delightful!" says when she sees me. "Sir is going to love this". "How does it feel?" I confess that it hurts. "Poor baby! Let me take those cups off there for you" and she does. "Now. I think Anthony could do with a tip. I'll let you to sort that" and she takes her cup and departs.

I didn't need telling what to do. I got on my knees and ran my hands up Anthony's thighs. He undid his trousers, reached in and slid out his cock. It started to stiffen and bob in front of my face. I lent forward and kissed the tip, swirling my tongue around slowly. Then, I licked from the base of his cock to the tip, again swirling my tongue as I went. I took the first couple of inches in my mouth. I had learnt by now that women rarely took much more that, instead they disguised how much they took by where they placed their hands. I placed my hands strategically and worked those two inches. The most important thing is finding the right rhythm and Anthony's was easy to find. I settled into a pace where I knew I was in control. I could have made him cum in 30 seconds - or had him on edge for 30 minutes. I felt his hand go to the back of my head and he moaned. He was controlling the rhythm somewhat now. I heard him groan. His cock pulsed. I was enjoying giving him pleasure, I couldn't deny it. He started fucking my mouth faster, sliding his cock in and out until I felt it. I felt his cock pulse hard and his cum pour into my mouth. I swallowed as much as I could, but some did run down my chin and drip on my special tray; I could help thinking I'll likely get spanked for that....

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4Leather4Leather8 months ago

Know how my clover clamps are on my nipples. Pulling on nipple rings might feel different. I’m sure it would not be a good time.

woodseaveswoodseavesover 1 year ago

Oooh, that's rather painful for "you", the maid.

The nipple rings are a nice touch as the are revealed through the peep holes.

I love your character, wish I could be invited to visit

AnonymousAnonymousover 2 years ago

I like it but I don't envy the pain on his poor nipples. Nipples should be his 1 source of pleasure. They are for me.

AnonymousAnonymousover 2 years ago

Love this, glad to see you have older work. Thanks for the great post.

AnonymousAnonymousover 2 years ago

Great new story, glad to see you're back writing, hope there is more to come.

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